The production of aniline derivatives of the general formula (3) from halogen-substituted aminophenol derivatives of the general formula (1) usually starts with aminophenol derivatives in which the amino group suspected of doing harm to the reaction is protected with a suitable protective group and comprises the steps of alkylating the starting material on the oxygen atom in the presence of a base and thereafter removing the protective group. For instance, as exemplified by Reaction Scheme (I) given below, phenol (5) having the amino group protected as a carbamate group is alkylated and the ester is then hydrolyzed under basic conditions to produce an aniline derivative (see, for example, Reference Examples in Japanese Patent Public Disclosure Nos. Hei. 4-145071 and Hei. 4-164067) (see under Reference Examples 1 and 2 to be described later in this specification): ##STR5##
The production of aniline derivatives of the general formula (3) from bis(amino-substituted phenyl)carbonate derivatives of the general formula (4) usually starts with aminophenol derivatives that are prepared by first protecting with a suitable protective group the amino group suspected of doing harm to the reaction and by then hydrolyzing only the carbonate bond without impairing the protective group and the production process comprises the steps of alkylating the starting material on the oxygen atom in the presence of a base and thereafter removing the protective group. For instance, as exemplified by Reaction Scheme (II) given below, bis(5-alkoxycarbonyl-amino-2-chloro-4-fluorophenyl)carbonate (8) having the amino group protected as an alkyl carbamate group is hydrolyzed selectively to a phenol derivative (9), then alkylated and, thereafter, the carbamate group is hydrolyzed under basic conditions to produce an aniline derivative (3) (see, for example, Japanese Patent Public Disclosure No. Hei 5-17411 or Hei. 5-43525): ##STR6##
Thus, the prior art methods described above require additional steps for introducing and removing the amino protective group and this is disadvantageous from an economic viewpoint since not only is the reaction process extended but it is also necessary to use auxiliary materials as appropriate for the respective steps.